Few of life’s pleasures are more satisfying in combination than jazz and cocktails. The two have enjoyed a long, productive relationship, dating back at least to the 1920s, when illicit speakeasies jumped and swayed to the sounds of live jazz. The pair may have reached their cultural zenith in the nightclubs of the mid-20th century; the image of men in sharp suits and women in glamorous dresses, sipping martinis while a crooner and big band fill the room with swing music and sultry classics, remains iconic.
Jazz and cocktails have never truly been out of style, though their popularity has certainly ebbed and flowed over the years. Today you can find exceptional craft cocktails in any number of Boston-area establishments, and there are plenty of places where you can hear some smokin’ jazz. If you’re looking for nightly jazz played by an ever-shifting lineup of locals, Wally’s is your best bet. If nationally renowned performers are your thing, there’s Scullers and Regattabar. Fashionable entries like the Beehive and Beat Hotel fall somewhere in the middle.

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Watertown’s Stellina probably isn’t even on your radar. That’s understandable – it’s a suburban Italian restaurant, not a jazz club, and they only have live jazz on Tuesday nights. But for me, Stellina hits the sweet spot – solid jazz, above-average cocktails, a cozy bar, affordable food options, and a laid-back atmosphere. (It’s also a 10-minute walk from my home, which doesn’t hurt.)

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Having served Watertown for nearly 30 years, Stellina is a bona fide institution. Their Italian cuisine has won awards from Boston Magazine, and their beautiful back patio provides for elegant dining beneath the stars. Walled off from the main dining room is Stellina’s bar area, with a 14-seat bar and several two-seat tables. Dark wood and red lighting give the space an intimate appearance, but the mood is decidedly casual.

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This is where the Noteworthy Jazz Ensemble, the house band since 2008, sets up around 6 p.m. every Tuesday. The quartet – sax, guitar, bass, and drums – seamlessly blends timeless standards like “Caravan,” “Black Orpheus,” “Moanin’,” and “A Foggy Day” with original numbers and off-the-cuff jams (you might even hear a Black Sabbath riff or two thrown in).

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Overall, it’s a laid-back affair. The band fields occasional requests from customers and chats with regulars during breaks. If you’re sitting close enough, you can hear them discussing which key to play a particular song in. The music isn’t so intense that it inhibits conversation, but it doesn’t fade into the background, either. And while you can hear the Ellington and Coltrane tunes from just about anywhere in the restaurant, the bar is the place to be if you’re a jazz fan.

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Obviously, it’s the best place to be for drinks, too. Italian restaurants may be better known for wine than for cocktails, but Stellina is the only place I know of in Watertown with a cocktail program of this caliber. The rotating drink menu reflects some of the broader trends in nearby Boston and Cambridge, updating classic cocktails with inventive twists and offering a few original concoctions with house ingredients.

The Cool-Manhattan is the quintessential partner for some cool jazz. It’s an appropriately straightforward Manhattan made with Maker’s 46 (aged a little longer than the flagship Maker’s Mark), Carpano sweet vermouth, bitters, and a Luxardo cherry.

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In a similar vein is the Cocktail Italiano, combining Old Overholt Rye, Amaro Montenegro, grapefruit bitters, and lemon syrup, garnished with a mint leaf. Dry and sour, a fresh, minty aroma accompanies every sip.

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The Hot Toddy has no doubt been a popular item in this hellish winter, and it demonstrates Stellina’s tendency to mix things up a bit with some of the supporting ingredients. Applejack brandy combines with lemon peel and a ginger- and chamomile-infused honey for a sweet, apple-forward drink with plenty of flavor. Warms the belly and the soul on a brisk night.

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The Cocktail 47 (named after Stellina’s address) is sort of a vodka-based riff on the Hemingway daiquiri. Made with Belvedere grapefruit vodka, maraschino liqueur, fresh grapefruit, and lime, there’s a lot going on in this one – a blast of sourness and a prominent grapefruit flavor.

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The Caipirinha Sour is a more recent addition to the menu, and one of the few missteps. This mix of cachaça, muddled lime, homemade sour mix, and fresh tangerine has all the right ingredients for a refreshing variation of traditional Brazilian cocktail, but it’s topped with a flat soda that mutes those great flavors.

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There are plenty more creative high points, though, like the simply titled “Pear.” Made with Belle de Brillet Pear Cognac, Grey Goose vodka, reduced pear, and vanilla nectar, it’s a soft, smooth drink that nonetheless packs a punch.

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The Ransom Citrus-Lavender combines Ransom Old Tom gin, a lemon cordial, and lavender-citrus infused agave. It’s dry and full-flavored, with a distinct citrus component and a delicate floral essence.

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The Royal Snap is an unusually complex rendering of a whiskey and ginger, made with the intriguing Whippersnapper Oregon whiskey, which has some gin-like botanical notes to it, along with muddled blood orange, homemade orange bitters, a ginger reduction, and ginger beer.

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For those craving something more straightforward, the Moscow Mule is simple and traditional – Tito’s Handmade vodka, ginger beer, and lime, served in the customary copper cup.

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My good friend and fellow barhopper/Watertown resident/jazz fan Mario and I have resolved to hit Stellina at least one Tuesday a month for this jazz-and-cocktail combo, and so far we have a perfect record in 2015. It’s an endeavor made easier by some fairly economical dinner selections. On the antipasti menu, the handmade sweet potato gnocchi, tossed with Gorgonzola, sage, and Parmesan, is generously sized and delicious. I’ve always been curious to try gnocchi made with sweet potato; it adds a nice dimension.

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There’s a selection of flatbreads that you can customize if you so desire. This smoked prosciutto, garlic, Fontina, and rosemary pizza, with hot sausage added, is becoming my go-to order.

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And if you’re craving something sweet, the Crème Brulee Napoleon tastes as good as it looks. Layered with phyllo pastry, caramel sauce, and toasted hazelnuts, it’s crunchy and surprisingly light (I’m not necessarily speaking form a caloric standpoint here).

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Concluding with such a beautifully presented dessert seems fitting, in a way. Nearly everything about Stellina reveals a fondness for performance and artistry – from hosting live jazz to serving contemporary craft cocktails with lemon cordials, infused syrups, and fruit reductions. In addition to the weekly jazz nights are occasional opera nights, author nights, and wine tastings. Even the blog on their website is well written and regularly updated. To me that signals a creative spirit, and whether it’s in a restaurant in Watertown, a jazz club in Boston, or a modern cocktail bar, that’s a great attribute to have.